Hi friend, i think you need to check your connection status first.
From IP Phone to analog:
The analog phones are configured via ATA, conected to a MGCP gateway or H323?
If H323, make sure that you have a route pattern in your CCM that is pointed to the analog phones
If MGCP, verfy the partition and CSS configuration.
From analog phone to IP Phone, if h323, verify that your have the dial-peer voice X voip pointed to the CCM ip address and dial plan, also verify that you have this commands in your gateway:
voice rtp send-recv
interface FastEthernet0/0
ip address 192.168.10.1 255.255.255.0
h323-gateway voip bind srcaddr 192.168.10.1
Hope this little comment help you
Best regards
David